Mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-one antifungal agents

ABSTRACT

Selected mono-5-substituted-3-chloro-4H-1,2,6 thiadiazin-4-ones having the general formula ##STR1## are described which are useful for control of fungal disease in plants.

This application is a continuation of application Ser. No. 904,828 filed May 11, 1978, now abandoned, in turn a division of Ser. No. 782,860, filed Mar. 30, 1977, now U.S. Pat. No. 4,097,594.

BACKGROUND OF THE INVENTION

The present invention relates to a method for controlling fungal disease in plants, to novel antifungal compositions, and to compounds useful for controlling fungi which attack agricultural and garden plants and seeds. More particularly, the invention relates to the use of a selected mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-one as an angifungal agent for controlling fungal disease in plants.

Geevers and Trompen disclosed the preparation 3,5-dichloro-4H-1,2,6-thiadiazin-4-one and its use as an intermediate to prepare various other 5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-ones including the 5-phenoxy derivative. J. Geevers and W. P. Trompen, Rec. Trav. Chim., 93, 270 (1974).

While 5-chloro and 5-phenoxy derivatives and the method for preparing them have been disclosed, the reference provides no indication of any biological activity. More particularly, there is no suggestion that the compounds of this invention have antifungal activity.

It has now been found that selected mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-ones, which are hereinafter described, exhibit excellent antifungal activity and are useful in providing control of fungal disease in agricultural crops by foliar, seed, and soil application.

SUMMARY OF THE INVENTION

The present invention thus provides (1) a method for controlling fungal disease in plants which comprises applying a selected mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-one, as defined below, to the locus where control is desired, (2) antifungal compositions for control of fungal disease in plants, and (3) certain novel compounds which are useful for control of fungi.

DETAILED DESCRIPTION

In accordance with a first aspect of the present invention, there is provided a method for controlling fungal disease in agricultural crops and other plants which comprises applying to the locus where control is desired an effective fungistatic or fungicidal amount of a mono-5-substituted-3-chloro-4H-1,2,6-thiadiazin-4-one of the formula ##STR2## in which X is halogen, phenoxy, naphthoxy or substituted phenoxy having the formula ##STR3## wherein each R group is a substituent independently selected from lower alkyl, halo, lower alkoxy, hydroxy, nitro, cyano, amino, carboxyl, lower acyl, lower acylamino, lower alkoxycarbonyl, carboxy(lower)alkyl, lower alkylureido, phenylureido, trihalomethyl, cyano(lower)alkyl, phenyl(lower)alkoxycarbonyloxy, lower alkylaminocarbonyloxy, phenylaminocarbonyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl, wherein n has a value of 1 to 3 inclusive. However, when each R is halogen n may have a value of 1 to 5 inclusive.

More specifically there is utilized in the method the compounds of formula I in which X is halogen, phenoxy, naphthoxy or substituted phenoxy having the formula II wherein each R group is a substituent independently selected from:

A. lower alkyl, or halo;

B. hydroxy, lower alkoxy, nitro, cyano, amino, carboxyl, lower acyl, lower acylamino, lower alkoxycarbonyl, carboxy(lower)alkyl, lower alkylureido, phenylureido, trihalomethyl, cyano(lower)alkyl, phenyl(lower)alkoxycarbonyloxy, lower alkylaminocarbonyloxy, phenylaminocarbonyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl

wherein n has a value of 1 to 3 inclusive, except when each R is halogen n has a value of 1 to 5 inclusive, with the proviso that 0 to 2, preferably 0 or 1, R groups may be selected from group B.

Unless it is otherwise indicated, the term "lower" means having 1 to 6 carbon atoms, straight or branched chain, preferably 1 to 4 carbon atoms, and the term "halogen" means bromine, chlorine and fluorine or iodine.

In the method of this invention an effective fungistatic or fungicidal amount of active ingredient is applied to foliage or seeds of agricultural plants or to the soil in which the plants are growing or are to be planted, i.e., the locus where control is desired. When so applied, the compounds prevent fungal infection or inhibit further development of a pre-existing fungal disease.

In the method of this invention the selected antifungal agent may be applied as the technical material, or as a formulated product. Typical formulations include the antifungal agent in combination with an agriculturally acceptable carrier, preferably with a surface active agent, and optionally with other active ingredients. Suitable formulations include granules, powders, or liquids, the choice varying with the fungus and environmental factors present at the particular locus of infestation. Thus, the compounds may be formulated as granules of various sizes, as dusts, as wettable powders, as emulsifiable concentrates, as solutions, as dispersions, as controlled release compositions, and the like.

A typical formulation may vary widely in concentration of the active ingredient depending on the particular agent used, the additives and carriers used, other active ingredients, and the desired mode of application. With due consideration of these factors, the active ingredient of a typical formulation may, for example, be suitably present at a concentration of about 0.5% up to about 99.5% by weight of the formulation. Additives and carriers may comprise about 99.5% by weight to as low as about 0.5% by weight of the formulation. Surface active agents, if employed in the formulation, may be present at various concentrations, suitably in the range of 1% to 30% by weight.

The formulation may be used as such or diluted to a desired use dilution with a suitable diluent or carrier. The concentration of the active ingredient in use dilution is normally in the range of about 0.001% to about 4% by weight. Many variations of spraying, dusting, soil-incorporated, and controlled or slow release compositions in the art may be used by substituting or adding a compound of this invention into compositions known or apparent to the art.

The antifungal agents of this invention may be formulated and applied with other compatible active ingredients, including nematicides, insecticides, acaricides, other fungicides, plant regulators, herbicides, fertilizers, etc.

In applying the foregoing chemicals, whether alone or with other agricultural chemicals, an effective fungistatic or fungicidal amount of the active ingredient must be applied. While the application rate will vary widely depending on the choice of compound, the formulation and mode of application, the plant species being protected, and the planting density, a suitable use rate may be in the range of 0.05 to 5 kg/hectare, preferably 0.5 to about 4 kg/hectare.

The antifungal composition of this invention comprises a compound of formula I as defined above in admixture with an agriculturally acceptable carrier, preferably containing a compatible surface active agent.

Certain compounds of formula I, notably those in which X is chloro or phenoxy, are disclosed in the cited literature. The novel compounds of this invention are those in which X is other than halogen or phenoxy; that is, the compounds of formula I in which X is naphthoxy or substituted phenoxy having the formula II wherein each R group is a substituent independently selected from lower alkyl, halo, hydroxy, lower alkoxy, nitro, cyano, amino, carboxyl, lower acyl, lower acylamino, lower alkoxycarbonyl, carboxy(lower)alkyl, lower alkylureido, phenylureido, trihalomethyl, cyano(lower)alkyl, phenyl(lower)alkoxycarbonyloxy, lower alkylaminocarbonyloxy, phenylaminocarbonyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl wherein n has a value of 1 to 3 inclusive with the proviso that when each R is halogen n may have a value of 1 to 5 inclusive.

More specifically the novel compounds of this invention are those of formula I in which X is naphthoxy or substituted phenoxy having the formula II wherein each R group is a substituent independently selected from:

A. lower alkyl, or halo;

B. hydroxy, lower alkoxy, nitro, cyano, amino, carboxyl, lower acyl, lower acylamino, lower alkoxycarbonyl, carboxy(lower)alkyl, lower alkylureido, phenylureido, trihalomethyl, cyano(lower)alkyl, phenyl(lower)alkoxycarbonyloxy, lower alkylaminocarbonyloxy, phenylaminocarbonyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl

wherein n has a value of 1 to 3 inclusive, except when each R is halogen n has a value of 1 to 5 inclusive, with the proviso that 0 to 2, preferably 0 or 1, R groups may be selected from group B.

The compounds of this invention are prepared according to the teaching of Geevers and Trompen, supra; that is, by reacting 3,5-dichloro-4H-1,2,6-triadiazin-4-one with alcoholate ions, for example, sodium phenoxide. The following example are typical of the preparation of the compounds.

EXAMPLE I Synthesis of 3,5-Dichloro-4H-1,2,6-thiadiazin-4-one

A 50 ml flask was charged with 20 ml formic acid. The flask was purged witha stream of dry nitrogen. The nitrogen purge was continued while 6.3 g 3,4,4,5-tetrachloro-4H-1,2,6-thiadiazinone was added dropwise over 0.5 hour during which the temperature of the reaction mixture was maintained at 10±1° C. Following addition the reaction mixture was stirred at 10° C. for 2 hours then at room temperature for 64 hours, then poured into 60 ml. ice-water with stirring. The resulting mixture was filtered and the filter cake washed with water and dried to yield 2.2 g ofpale yellow 3,5-dichloro-4H-1,2,6-thiadiazin-4-one, mp 81°-82° C.

EXAMPLE II Synthesis of 3-Chloro-5-phenoxy-4H-1,2,6-thiadiazin-4-one

A sodium phenoxide solution was prepared by adding 1.0 g of sodium hydroxide to 2.4 g phenol in 25 ml of warm, distilled water. This mixture was stirred for 5 minutes then added to a suspension of 4.6 g of finely ground 3,5-dichloro4H-1,2,6-thiadiazin-4-one in 75 ml of distilled water in a 250 ml flask. This addition required 15 minutes during which the temperature rose to 32° C. After being stirred at room temperature for one hour, the orange mixture was filtered, and the filter cake was washed with water. Recrystallization from 100 ml of ethanol yielded 4.2 g of fluffy, pale yellow needles of 3-chloro-5-phenoxy-4H-1,2,6-thiadiazin-4-one, mp 121°-123° C. (Lit. mp 122.5°-123.5° C., J. Geevers and W. P. Trompen, supra.) An ir spectrum was consistent with the assigned structure.

Analyses calc'd for C₉ H₅ ClN₂ O₂ S: C 44.92; H 2.09; N11.64; Found: C 44.94; H 2.26; N 11.63.

The compounds of this invention which are set forth below have been synthesized in accordance with the typical preparatory method set forth inExamples I and II. An identifying number is provided for each compound. This compound number is used below in reporting biological data relating to the compound.

    ______________________________________                                         Compound No.  Identity                                                         ______________________________________                                         1             3,5-dichloro-4H--1,2,6-thia-                                                   diazin-4-one                                                     2             3-chloro-5-phenoxy-4H--                                                        1,2,6-thiadiazin-4-one                                           3             3-chloro-5-(4-methylphenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       4             3-chloro-5-(4-tert-butyl-                                                      phnoxy)-4H--1,2,6-thia-                                                        diazin-4-one                                                     5             3-chloro-5-(4-methoxyphenoxy)                                                  4H--1,2,6-thiadiazin-4-one                                       6             3-chloro-5-(4-n-butoxyphenoxy)-                                                4H--1,2,6-thiadiazin-4-one                                       7             3-chloro-5-(4-ethoxycarbonyl-                                                  phenoxy)-4H--1,2,6-thiadiazin-                                                 4-one                                                            8             5-(4-acetylaminophenoxy)-3-chloro-                                             4H--1,2,6-thiadiazin-4-one                                       9             3-chloro-5-(4-nitrophenoxy)-                                                   4H--1,2,6-thiadiazin-4-one                                       10            3-chloro-5-(4-cyanophenoxy)-                                                   4H--1,2,6-thiadiazin-4-one                                       11            3-chloro-5-(4-fluorophenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       12            3-chloro-5-(4-chlorophenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       13            3-chloro-5-(3-chlorophenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       14            3-chloro-5-(2-chlorophenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       15            3-chloro-5-(4-bromophenoxy)-                                                   4H--1,2,6-thiadiazin-4-one                                       16            3-chloro-5-(3,4-dichloro-                                                      phenoxy)-4H--1,2,6-thiadiazin-                                                 4-one                                                            17            3-chloro-5-(2,4-dichloro-                                                      phenoxy)-4H--1,2,6-thiadiazin-                                                 4-one                                                            18            3-chloro-5-(2,6-dichloro-                                                      phenoxy)-4H--1,2,6-thiadiazin-                                                 4-one                                                            19            3-chloro-5-(2,3-dichloro-                                                      phenoxy)-4H--1,2,6-thiadiazin-                                                 4-one                                                            20            3-chloro-5-(3,5-dichloro-                                                      phenoxy)-4H--1,2,6-thiadiazin-                                                 4-one                                                            21            3-chloro-5-(3-methylphenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       22            3-chloro-5-(2-methylphenoxy)-                                                  4H--1,2,6-thiadiazin-4-one                                       23            3-chloro-5-(2,4-dimethylphenoxy)-                                              4H--1,2,6-thiadiazin-4-one                                       24            3-chloro-5-(2,6-dimethylphenoxy)-                                              4H--1,2,6-thiadiazin-4-one                                       25            3-chloro-5-(3,5-dimethylphenoxy)-                                              4H--1,2,6-thiadiazin-4-one                                       26            5-(4-aminophenoxy)-3-chloro-                                                   4H--1,2,6-thiadiazin-4-one                                       27            5-(4-aminophenoxy)-3-chloro-                                                   4H--1,2,6-thiadiazine-4-one                                                    hydrochloride                                                    28            3-chloro-5-[4-(3-methylureido)-                                                phenoxy]-4H--1,2,6-thiadiazin-4-one                              29            3-chloro-5-[4-(3-phenylureido)-                                                phenoxy]-4H--1,2,6-thiadiazin-4-one                              30            3-chloro-5-(2,4,6-trichloro-                                                   phenoxy)-4H--1,2,6-thiadiazin-4-one                              31            3-chloro-5-(pentachlorophenoxy)-                                               4H--1,2,6-thiadiazine-4-one                                      32            3-chloro-5(1-naphthoxy)-                                                       4H-1,2,6-thiadiazin-4-one                                        33            3-chloro-5-(bromophenoxy)-                                                     4H-1,2,6-thiadiazin-4-one                                        34            3-chloro-5-(2-bromophenoxy)-                                                   4H-1,2,6,-thiadiazin-4-one                                       35            3-chloro-5-(4-hydroxyphenoxy)-                                                 4H-1,2,6-thiadiazin-4-one                                        36            3-chloro-5-[methylamino-                                                       carbonyloxy)phenoxyl]-4H-                                                      1,2,6-thiadiazin-4-one                                           37            3-chloro-5-[4-(phenylamino-                                                    carbonyloxy)phenoxy]-4H-                                                       1,2,6,-thiadiazin-4-one                                          38            3-chloro-5-[4-(phenyl                                                          methoxycarbonyloxy)phenoxyl]-                                                  4H-1,2,6-thiadiazin-4-one                                        39            3-chloro-5-[(4-methyl-                                                         thio)phenoxy]-4H-                                                              1,2,6,-thiadiazin-4-one                                          40            3-chloro-5-[(4-methyl-                                                         sulfinyl)phenoxy]-4H-                                                          1,2,6,-thiadiazin-4-one                                          41            3-chloro-5-[(4-methyl-                                                         sulfonyl)phenoxy]-4H--                                                         1,2,6-thiadiazin-4-one                                           42            3-[(3-N--acetylamino)-                                                         phenoxy]-5-chloro-4H--                                                         1,2,6-thiadiazin-4-one                                           43            3-[(2-acetylamino)-                                                            phenoxy]-5-chloro-4H--                                                         1,2,6-thiadiazin-4-one                                           44            3-chloro-5-[(3-trifluoro-                                                      methyl)phenoxy]-4H--1,2,6-                                                     thiadiazin-4-one                                                 45            3-(2-carboxymethylphenoxy)-                                                    5-chloro-4H--1,2,6-thiadiazin-                                                 4-one                                                            46            3-chloro-5-[(4-cyanomethyl)-                                                   phenoxy]4H--1,2,6-thiadiazin-                                                  4-one                                                            47            3-(4-acetylphenoxy)-5-chloro-                                                  4H--1,2,6-thiadiazin-4-one                                       48            3-(3-acetylphenoxy)-5-chloro-                                                  4H--1,2,6-thiadiazin-4-one                                       49            3-(2-acetylphenoxy)-5-                                                         chloro-4H--1,2,6-thiadiazin-                                                   4-one                                                            50            3-(4-carboxyphenoxy)-5-                                                        chloro-4H--1,2,6-thiadiazin-                                                   4-one                                                            51            3-chloro-5-[(2-chloro-5-                                                       methoxy)phenoxy]-4H--                                                          1,2,6-thiadiazin-4-one                                           52            3-chloro-5-[(3-chloro-5-                                                       methoxy)phenoxy]-4H--                                                          1,2,6-thiadiazin-4-one                                           53            3-chloro-5-(2-chloro-4-                                                        nitrophenoxy)-4H--                                                             1,2,6-thiadiazin-4-one                                           54            3-chloro-5-(4-chloro-3-                                                        methylphenoxy)-4H--                                                            1,2,6-thiadiazin-4-one                                           55            3-chloro-5-(4-chloro-2-                                                        methylphenoxy)-4H--                                                            1,2,6-thiadiazin-4-one                                           56            3-chloro-5-[(2-chloro-5-                                                       methyl)phenoxy]-4H--                                                           1,2,6-thiadiazin-4-one                                           57            3-[(2-bromo-4-methyl)-                                                         phenoxy]-5-chloro-4H--                                                         1,2,6-thiadiazin-4-one                                           58            3-chloro-5-[(2-chloro-                                                         4,5-dimethyl)phenoxy]-4H--                                                     1,2,6-thiadiazin-4-one                                           59            3-chloro-5-[(4-chloro-                                                         3,5-dimethyl)phenoxy]-4H--                                                     1,2,6-thiadiazin-4-one                                           60            3-[(4-bromo-3,5-dimethyl)-                                                     phenoxy]-5-chloro-4H--                                                         1,2,6-thiadiazin-4-one                                           61            3-[(4-acetyl-3,5-dimethoxy)-                                                   phenoxy]-5-chloro-4H--                                                         1,2,6-thiadiazin-4-one                                           ______________________________________                                    

The following examples demonstrate the practice of the present invention. The test organisms used in these examples, together with an identifying code which are in the tables to identify each organism, are as follows:

    ______________________________________                                         AS = Alternaria solani                                                                            PO = Pyricularia oryzae                                     BC = Botrytis cinerea                                                                             PU = Pythium ultimum                                        CC = Cladosporium cucumerinum                                                                     RS = Rhizoctonia solani                                     EP = Erysiphe polygoni                                                                            SF = Sclerotinia fructicola                                 PS = Fusarium solani                                                                              UP = Uromyces phaseoli                                      HO = Helminthosporium oryzae                                                                      VI = Venturia inaequalis                                    PI = Phytophthora infestans                                                    ______________________________________                                    

EXAMPLE III Spore Germination Tests

The test chemical was dissolved or suspended in acetone in an amount such that 0.8 ml of the resulting suspension or solution, mixed with 40 ml water agar produced a water agar solution containing 40, 10, 2.5 and 1 ppmof test chemical. The resulting agar solution, at 50° C., was then divided equally between two sterile petri dishes, each having four separated quadrants, and allowed to solidify. Three quadrants of each dishwere flooded with 0.1 ml of a spore suspension in sterile water. Spores of two pathogens, Erysiphe polygoni and Uromyes phaseoli, from infected plantleaves, were brushed on the remaining two quadrants. The tests were then incubated 48 hours, at 24° C.

Readings were then taken and the percentage of germinated spores calculated. From this percentage, a spore germination rating was assigned as follows:

    ______________________________________                                         Germination     Rating                                                         ______________________________________                                          0-10           0                                                              10-40           1                                                              40-60           2                                                              60-80           3                                                               80-100         4                                                              ______________________________________                                    

Table I reports the inhibitory effect of these test compounds on spore germination and demonstrates improvement over benomyl which was used as a standard for comparison. In Table I, the lower the numeral used as a rating, the more effective the compound.

EXAMPLE IV Mycelial Growth Tests

Aliquots of previously prepared solutions of active ingredient in acetone were added to tubes containing 20 ml of sterile, melted potato dextrose agar that had been cooled to 50° C. to provide mixtures of 40, 20, 10, 5 and 2.5 ppm. The tubes were shaken to ensure thorough mixing of the chemical with the agar, and the mixture poured into petri dishes having 4 quadrants to solidify. Each quadrant was inoculated with a 4 mm diameter disc of agar containing mycelium of the test fungi and incubated at 25° C. for 72 hours during which the samples were alternately exposed to light for 12 hours and to darkness for 12 hours. Growth was measured at the end of the incubation period by measuring the diameter of each fungus colony. Two measurements of the diameter, perpendicular to each other, were taken and the values averaged. Data are reported as percent inhibition (%I) by the following formula: ##EQU1##Captan and chlorothalonil were used as standards for comparison. The results reported in Table II indicate that the test compounds were generally more active than the standards.

EXAMPLE V

The compounds of this invention were tested for crop disease control to determine the basic types of antifungal activity they exhibit.

A. Foliar Protective Activity

The foliage of a tomato plant in the four leaf stage and a pinto bean in the primary leaf stage was sprayed with the test chemicals at a concentrations of 150 ppm on a weight/volume basis, and the plant allowed to dry overnight.

Sporangia of Phytophthora infestans (late blight fungus) were harvested from cultures grown on lima bean agar for 10 to 14 days. A water suspension of sporangia (2×10⁵ sporangia/ml) was incubated at 12° C. for two hours in order to provide a zoospore suspension. Spores of Uromyces phaseoli (bean rust fungus) were collected from diseased plants and a 2% spore powder mixture prepared using ABB Pyrax talc as a diluent.

The tomato plants were inoculated in a spray hood with the zoospore suspension, then immediately incubated in a humidity chamber at 100% relative humidity at 18°-20° C. for four to five days. The bean plants were inoculated by dusting the spore powder onto the leaves. This was accomplished by placing the spore powder in a cheesecloth bag andshaking the bag over the leaves. The inoculated plants were placed in the humidity chamber at 100% relative humidity and 21° C. for 24 hours and then placed in the greenhouse for four to six days until disease symptoms developed.

The percent disease control was then determined by comparing the disease incidence in treated plants and untreated check plants. Results reported in Table III demonstrate the efficacy of the compounds tested in preventing tomato late blight and bean rust when applied to foliage of uninfected plants at 150 ppm prior to disease infestation.

B. Foliar Curative Tests

In the curative tests the plants were inoculated with the appropriate pathogen 24 hours before chemical treatment. The following host-parasite combinations were used:

    ______________________________________                                         PLANT        FUNGUS          DISEASE                                           ______________________________________                                         Phaseolus vulgaris L.                                                                       Uromyces phaseoli Link                                                                         bean rust                                         Phaseolus vulgaris L.                                                                       Erysiphe polygoni DC                                                                           bean powdery                                                                   mildew                                            Beta vulgaris                                                                               Cercospora beticola                                                                            sugar beet                                                                     leaf spot                                         Oryzae sativa L.                                                                            Pyricularia oryzae                                                                             rice blast                                        ______________________________________                                    

Spores of bean rust and bean powdery mildew were obtained from diseased plants. Spores of Cercospora beticola and Pyricularia oryzae were harvested from petri dish cultures. C. beticola was grown on potato dextrose agar and P. oryzae on a glucose yeast extract medium. The cultures were grown at 25° C. for 10 days.

Beans (c.v. `Pinto`) were inoculated with rust as described in Example IV-A. Beans (c.v. `Bountiful`) at primary leaf stage were inoculated with powdery mildew by shaking diseased leaves over the test plants, thereby creating a spore deposit on leaves of the test plants. Sugar beets and rice were inoculated by spraying a water suspension of spores of the appropriate pathogen on the foliage.

All of the plants except those inoculated with bean powdery mildew were incubated in the moisture chamber (21° C.) for 24 hours. The bean powdery mildew inoculated plants were incubated in the greenhouse.

The test chemical was sprayed on the foliage of the plants at 150 ppm 24 hours after inoculation. The bean and rice plants were removed from the moisture chamber and allowed to dry before chemical treatment. After treatment the plants were incubated in the greenhouse for 6-10 days. The sugar beets were sprayed while still wet, after which they were immediately returned to the moisture chamber for two days and then to the greenhouse for 10-14 days.

The results tabulated in Table III demonstrate curative activity when applied after infection of the plant.

C. Soil/Seed Treatment

Containers having a volume of about 0.25 l. were 2/3 filled with topsoil and 25 cucumber c.v. [Straight Eight` seeds deposited on the soil surface of each pot. A suspension containing 150 ppm of the test chemical was poured over the seeds and into the soil in sufficient quantity to provide 3.75 to 3.8 mg active ingredient per pot.

Fungi used in this test were Pythium ultimum and Rhizoctonia solani. These fungi were each grown on potato dextrose agar for three to six days. The agar plus mycelium was then minced in a blender with water and 10 ml of the resulting slurry of minced mycelium poured over the seeds.

Following inoculation approximately 15 mm of topsoil was spread over the seeds, the container capped and incubated at 4° C. in darkness for three days, then transferred to a greenhouse (27° C.) for 10-14 days, at which time stand counts were made. Captan was used as a standard for comparison. Based on stand counts on Efficacy Index was calculated foreach test chemical as follows: ##EQU2##

The results, set forth in Table III, show that many of the compounds testedwere considerably more effective than captan for treatment of Cucumber damping-off complex.

In a similar manner the soil around a bean seedling was drenched with a sufficient amount of 150 ppm suspension of test chemical to provide 3.8 mgactive per pot. Twenty-four hours later the soil was inoculated with a suspension of minced mycelium of Fusarium solani. The inoculated plants were then placed in a greenhouse, evaluated after fourteen days, and percent control of root rot damage calculated. The results, reported in Table III, indicate only a few of the compounds tested are effective in treating Bean Root Rot but that these provide a high degree of control.

                  TABLE I                                                          ______________________________________                                         RESULTS OF IN VITRO SPORE GERMINATION                                          INHIBITION TESTING                                                             CPD    Conc.   Spore Germination Rating                                        No.    ppm     BC     PO   VI  AS   CC   PI  EP   UP                           ______________________________________                                          2     40      0      0    0   0    0    0   1    0                                   10      0      0    0   0    0    1   3    0                                   2.5     4      1*   2*  0    4    1   4    2                                   1.0     4      3    4   4    4    0   4    2                             3     40      0      0    0   0    0    0   1    0                                   10      0      0    0   0    0    0   4    0                                   2.5     4      4    4*  4    4    2   4    1*                                  1.0     4      0    4   4    4    3   4    4                             4     40      2*     0    0   4    0    0   0    0                                   10      4      0    0   4    0    0   2    0                                   2.5     4      4    4   4    4    3   3    4                                   1.0     4      4    4   4    4    4   4    4                             5     40      0      0    0   0    0    0   0    0                                   10      1*     0    0   0    0    2   4    0                                   2.5     4      1*   0   0    4    2   4    1                                   1.0     4      4    3*  2    4    2   4    1                             6     40      4      0    0   4    0    0   0    0                                   10      4      2*   0   4    0    0   0    0                                   2.5     4      1*   0   4    0    0   0    0                                   1.0     4      2*   1   4    0    2   0    1                             7     40      3      1*   0   4    1    0   0    0                                   10      2      1*   0   4    0    0   2    0                                   2.5     3      1*   0   4    0    0   3    0                                   1.0     4      1    0   4    0    0   4    0                             8     40      4      0    0   0    0    0   2    0                                   10      4      0    2*  2    0    0   4    0                                   2.5     4      3    3   2    3    4   4    4                                   1.0     4      4    4   3    4    4   4    4                             9     40      0      0    0   0    0    0   4    0                                   10      0      0    0   0    0    0   4    0                                   2.5     0      0    0   0    0    0   4    0                                   1.0     0      0    0   0    0    0   4    0                            10     40      0      0    0   1    0    1   1    0                                   10      0      0    0   1    0    0   2    0                                   2.5     0      0    0   1    0    0   2    0                                   1.0     2      0    0   1    0    0   2    0                            11     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     1      0    1   0    0    0   0    0                                   1.0     4      3    4   4    0    4   0    4                            12     40      0      0    0   0    0    0   0    0                                   10      0      0    1*  0    0    1   2    0                                   2.5     2      0    1*  0    0    1   4    1                                   1.0     0      0    1   3    2    1   4    1                            13     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     4      0    0   0    0    0   2    0                                   1.0     4      3    1*  2    2    0   4    0                            14     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   2    0                                   2.5     0      0    0   2*   0    0   4    0                                   1.0     3      3    0   3    4    0   4    0                            15     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     1      1    0   1    0    1   1    0                                   1.0     4      0    0   4    0    0   4    1                            16     40      1*     0    0   0    0    0   4    0                                   10      0      0    0   0    0    0   1    0                                   2.5     1*     0    0   0    0    0   3    0                                   1.0     4      0    0   1    0    1   4    1                            17     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     0      0    0   1    0    0   1    0                                   1.0     4      0    0   2*   4    3   3    0                            18     40      0      0    0   0    0    0   0    0                                   10      0      0    0   1*   0    0   0    0                                   2.5     1*     2    0   2*   0    0   1    0                                   1.0     4      4    1   3    4    3   2    0                            19     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     1      0    0   3    0    0   1    0                                   1.0     4      3    1*  3    2    3   3    0                            20     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     0      0    0   0    0    0   0    0                                   1.0     4      1    0   2    0    0   3    0                            21     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   2    0                                   2.5     3      0    3   1*   0    1   3    2                                   1.0     4      4*   4   3    1    4   4    4                            22     40      0      0    0   0    0    0   1    0                                   10      0      0    0   0    0    0   3    1                                   2.5     0      0    0   0    0    0   4    2                                   1.0     2      2    0   3    0    0   4    4                            23     40      0      0    0   0    0    0   1    0                                   10      4*     0    1   0    0    2   3    1                                   2.5     4*     0    3   3    1    2   4    4                                   1.0     4      4    4   3    4    4   4    4                            24     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    1   0    0                                   2.5     1      0    0   1*   0    2   1    0                                   1.0     3      3    2   1    0    4   3    1                            25     40      0      0    0   0    0    0   0    0                                   10      0      0    2   0    0    0   0    1                                   2.5     1*     0    0   2    0    1   4    2                                   1.0     2      3    4   4    0    4   4    4                            26     40      0      0    1   0    0    2*  4    2                                   10      0      0    4   0    0    4   4    4                                   2.5     0      2*   4   3    0    4   4    3                                   1.0     0      4    4   4    1    4   4    2                            27     40      0      0    0   0    0    2   4    0                                   10      0      0    0   3*   0    4   4    1                                   2.5     0      0    0   4    0    3   4    1 - 1.0 1* 4 0 4 1 4 4 4                                                       2                            28     40      0      1    3   4    0    2   4    2                                   10      0      4    2   4    1    4   4    2                                   2.5     1      4    4   4    2    4   4    2                                   1.0     4      4    4   4    2    4   4    4                            29     40      2*     2*   0   4    1    3   1    0                                   10      2*     4    4   4    2    4   4    2                                   2.5     3      4    4   4    2    4   4    2                                   1.0     3      4    4   4    2    4   4    4                            30     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     0      0    0   0    0    1   0    0                                   1.0     0      3    1   3    0    4   1    0                            31     40      0      0    0   0    0    2   0    0                                   10      1*     0    0   0    0    2   1    0                                   2.5     1*     0    0   1    0    3   0    0                                   1.0     1*     0    0   4    0    4   0    0                            32     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     0      0    0   1    0    1   2    0                                   1.0     2      2    3   3    0    3   2    3                            33     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     3      0    0   0    0    0   0    0                                   1.0     4      2*   0   1*   0    0   0    0                            34     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     0      0    0   1*   0    1   2    0                                   1.0     2*     1*   0   4*   1*   4   0    0                            35     40      3*     0    --  0    0    0   1    0                                   10      4      0    --  3*   3*   0   2    0                                   2.5     4      0    --  4*   0    0   4    0                                   1.0     4      2    --  4    4    4   4    0                            36     40      2      0    --  0    0    0   1*   0                                   10      4      0    --  2*   --   4   1*   0                                   2.5     4      2*   --  4    3*   4   3*   2                                   1.0     4      4    --  4    4    4   4*   4                            37     40      4      2    --  3    0    4   3    1                                   10      4      0    --  4    0    4   4    1                                   2.5     4      3    --  4    1*   4   4    2                                   1.0     4      4    --  4    0    4   4    4                            38     40      3      2    --  4    3    3   4    2*                                  10      4      2    --  4    3    4   4    3                                   2.5     4      3    --  4    4    4   4    4                                   1.0     4      4    --  4    4    4   4    4                            39     40      3      0    --  0    0    3   0    0                                   10      4      1    --  2    0    3   2    2                                   2.5     4      1    --  3    0    4   1    2                                   1.0     4      2    --  4    1    4   2    2                            40     40      3      1    --  0    0    0   1    1                                   10      4      4    --  1    0    2   4    1                                   2.5     4      3    --  2    0    3   4    2                                   1.0     4      4    --  4    4    4   4    3                            41     40      3      0    --  0    0    0   0    0                                   10      4      0    --  0    0    0   1    0                                   2.5     0      3    --  2    0    2*  2    1                                   1.0     0      4    --  4    0    4   2    4                            42     40      1*     0    1   2*   0    0   4    0                                   10      4      3    4*  4    3    3   4    1                                   2.5     4      4    4*  4    4    4   4    3                                   1.0     4      4    4   4    4    4   4    4                            43     40      3      1    2   3    0    2   1    4                                   10      4      4    4   4    2    4   4    4                                   2.5     4      4    4   4    4    4   4    4                                   1.0     4      4    4   4    4    4   4    4                            44     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     3*     0    1*  1*   0    0   1    0                                   1.0     4      1    1*  4    1*   2   3    1*                           45     40      2*     1*   0   2*   0    0   2    2                                   10      4      4    4   4    2    0   4    4                                   2.5     4      4    4   4    4    4   4    4                                   1.0     4      4    4   4    4    4   4    4                            46     40      0      0    --  0    0    0   4    0                                   10      3*     0    --  2*   0    1*  4    0                                   2.5     3*     0    --  2*   0    1*  4    0                                   1.0     4      0    --  4    4    4   4    1                            47     40      0      0    0   0    0    0   1    0                                   10      0      0    0   0    0    0   4    0                                   2.5     1      0    0   0    0    0   4    0                                   1.0     4      1    1*  2    0    0   4    0                            48     40      0      0    0   0    0    0   2    0                                   10      0      0    0   0    0    0   2    0                                   2.5     4      1*   1*  3    0    0   4    0                                   1.0     4      3*   3*  4    0    0   4    0                            49     40      0      0    0   0    0    1   2    0                                   10      0      0    1   2*   0    1   2    0                                   2.5     1*     1    4   3*   0    1   4    1                                   1.0     1      2*   4   4    0    3*  4    4                            50     40      4      0    0   4    2    0   2    0                                   10      4      4    4   4    3    0   4    2                                   2.5     4      4    4   4    3    2   4    4                                   1.0     4      4    4   4    3    4   4    4                            51     40      0      0    --  0    0    0   0    0                                   10      0      0    --  1*   0    1   0    0                                   2.5     3      0    --  4    0    3   4    0                                   1.0     4      3    --  4    3    4   4    0                            52     40      0      0    --  0    0    0   0    0                                   10      0      0    --  0    0    0   0    0                                   2.5     3*     0    --  3*   0    0   2    0                                   1.0     4      4    --  4    4    4   4    2                            53     40      0      0    --  0    0    0   0    0                                   10      0      0    --  0    0    0   0    0                                   2.5     0      0    --  0    0    0   1    0                                   1.0     3      2    --  2    0    1   2    1                            54     40      1*     0    0   4    0    0   0    0                                   10      2      0    0   4    0    0   0    0                                   2.5     4      0    0   4    0    0   0    0                                   1.0     4      0    1*  4    2    1*  2    0                            55     40      1*     0    0   0    0    0   1*   0                                   10      1*     0    0   1*   0    0   0    0                                   2.5     3      0    0   2*   1    0   0    0                                   1.0     4      1*   1*  4    2    1*  1*   0                            56     40      0      0    --  0    0    0   0    0                                   10      0      0    --  0    0    0   0    0                                   2.5     0      0    --  3*   0    0   2    0                                   1.0     4      0    --  4    4    4   4    1                            57     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     1*     2*   0   2*   0    1*  0    0                                   1.0     3      0    2*  4    3    4   4    0                            58     40      0      0    0   0    0    0   0    0                                   10      0      0    0   0    0    0   0    0                                   2.5     0      0    1*  3*   0    2*  0    0                                   1.0     3      4    2*  4    3    3*  4    2*                           59     40      3*     0    1*  4    0    0   1*   0                                   10      4      0    0   4    0    1*  1*   0                                   2.5     4      0    1*  4    0    1   1*   2                                   1.0     4      0    1*  4    1*   4   2*   2                            60     40      3*     0    0   3*   0    0   0    0                                   10      3*     0    0   4    0    1*  1*   0                                   2.5     3*     0    1*  4    0    2*  1*   0                                   1.0     4      0    2*  4    0    4   2*   0                            61     40      2      1    --  2    0    0   0    0                                   10      3      2    --  2    0    3   1    2                                   2.5     4      4    --  3    0    4   1    1                                   1.0     4      4    --  4    4    4   1    2                            Benomyl                                                                               40      4*     0    0   4    0    1   0    0                                   10      4*     3*   0   4    3*   0   0    1*                                  2.5     4*     4*   3*  4    4*   2   2    1                                   1.0     4*     4*   3   4    4*   2   2    4                            ______________________________________                                         *Abortive Germ Tubes                                                      

                  TABLE II                                                         ______________________________________                                         RESULTS OF IN VITRO MYCELIAL                                                   GROWTH INHIBITION EVALUATION                                                          Percent Fungus Growth Inhibition                                        CPD  Conc.                                                                     No.  ppm.    AS     PS   SF   PO   PU   RS   HO   CC                           ______________________________________                                         1    10      100    100  100  82   100  100  100  --                                5       100    100  100  42   0    64   100  --                                2.5     100    85   100  27   0    100  100  --                           2    40      100    100  100  100  100  78   100  100                               20      100    76   100  56   100  100  100  100                               10      100    65   67   26   42   42   64   58                                5       75     53   52   22   0    0    55   46                           3    40      100    65   100  93   100  100  100  100                               20      100    65   94   41   100  56   100  100                               10      63     53   67   41   100  20   64   67                                5       19     35   27   19   20   0    55   58                           4    40      17     8    0    19   0    0    33   45                                20      0      0    4    0    0    0    24   27                                10      13     0    0    0    20   0    0    9                                 5       13     0    0    0    0    0    0    0                            5    40      100    71   73   63   100  64   100  100                               20      100    6    67   48   76   38   73   100                               10      100    35   42   22   42   0    64   75                                5       100    18   27   4    0    0    50   50                           6    40      21     13   67   19   22   20   48   45                                20      13     0    0    19   0    0    0    0                                 10      0      0    67   0    0    0    0    0                                 5       8      0    0    15   0    0    0    0                            7    40      92     88   100  81   100  76   100  100                               20      75     69   100  77   80   53   100  100                               10      75     54   100  65   29   33   43   36                                5       54     42   54   19   11   7    48   9                            8    40      86     31   60   74   100  42   81   100                               20      69     31   51   48   100  7    0    67                                10      41     41   0    0    100  0    33   58                                5       38     3    0    23   0    0    24   50                           9    40      100    100  100  93   100  78   100  100                               20      100    53   100  70   71   69   86   92                                10      63     76   76   48   80   42   82   75                                5       31     65   58   22   0    13   50   54                           10   40      92     75   100  77   64   100  100  100                               20      92     50   100  58   42   100  100  100                               10      79     33   33   19   24   13   52   45                                5       54     17   42   19   11   9    57   9                            11   40      100    75   100  62   100  91   100  100                               20      100    83   100  54   82   76   100  100                               10      83     33   100  38   18   38   100  64                                5       63     17   100  15   0    0    62   27                           12   40      100    100  100  85   100  100  100  100                               20      63     65   100  59   100  64   100  71                                10      31     59   82   30   100  58   59   58                                5       31     71   64   19   42   20   59   63                           13   40      100    100  100  100  100  76   81   100                               20      86     72   100  74   89   69   76   100                               10      59     50   67   42   73   53   86   67                                5       45     38   51   44   31   24   71   58                           14   40      100    100  100  100  100  91   100  100                               20      100    100  87   55   100  76   100  100                               10      79     100  64   26   53   56   71   50                                5       86     44   47   23   31   53   71   67                           15   40      75     83   88   58   76   53   100  100                               20      66     42   83   50   80   38   95   82                                10      66     42   83   19   76   38   90   55                                5       54     0    92   12   47   13   57   9                            16   40      50     41   67   41   56   69   82   75                                20      56     47   67   48   47   31   55   67                                10      50     47   67   48   11   31   55   54                                5       38     53   64   41   7    29   64   58                           17   40      100    100  100  71   100  76   100  100                               20      93     100  96   29   100  76   100  100                               10      72     75   76   48   80   53   100  100                               5       79     50   62   29   42   40   100  100                          18   40      84     75   100  48   100  87   100  100                               20      90     75   89   48   100  76   100  100                               10      90     50   64   32   60   56   86   100                               5       69     41   51   26   13   42   86   83                           19   40      100    100  100  87   100  82   100  100                               20      90     81   100  68   100  69   100  100                               10      62     66   76   48   80   47   90   100                               5       62     50   64   39   20   29   100  100                          20   40      83     69   87   74   100  78   100  100                               20      59     100  84   68   91   76   100  100                               10      59     66   73   74   91   58   100  100                               5       59     59   60   48   53   51   100  100                          21   40      100    100  100  58   100  100  100  85                                20      75     58   100  50   100  87   100  69                                10      63     62   100  33   33   64   86   38                                5       75     33   100  33   27   53   64   38                           22   40      100    100  100  63   100  100  100  92                                20      100    83   100  54   96   91   100  69                                10      88     67   100  33   64   62   100  46                                5       63     17   24   21   20   42   100  31                           23   40      100    100  100  58   100  78   100  100                               20      100    100  100  46   71   73   100  81                                10      81     33   100  42   69   53   100  38                                5       63     17   82   21   62   20   100  27                           24   40      100    100  100  100  100  100  100  100                               20      100    100  100  63   64   82   100  100                               10      88     83   100  42   47   64   100  65                                5       100    33   100  21   0    20   86   46                           25   40      88     100  100  63   100  78   100  100                               20      81     100  100  54   100  80   100  77                                10      75     100  100  58   47   64   100  50                                5       69     50   82   33   0    20   79   27                           26   40      100    42   100  100  100  76   100  77                                20      100    17   100  90   13   42   57   49                                10      80     33   66   48   0    53   57   49                                5       60     13   17   0    0    0    43   37                           27   40      87     42   86   81   80   64   57   54                                20      80     13   28   0    0    24   43   49                                10      73     8    21   24   0    31   21   40                                5       47     13   0    24   0    0    0    31                           28   40      70     13   62   90   100  47   64   60                                20      50     17   0    52   91   24   21   26                                10      47     17   28   24   80   47   29   26                                5       40     0    17   24   0    20   29   14                           29   40      47     13   7    0    0    29   0    31                                20      37     0    0    0    0    0    14   14                                10      30     0    31   14   0    31   0    11                                5       47     0    28   19   0    0    0    14                           30   40      90     100  97   90   100  80   100  100                               20      81     90   97   84   96   69   100  100                               10      67     81   87   71   71   62   100  100                               5       29     52   50   10   20   42   59   75                           31   40      67     58   52   57   0    76   100  69                                20      48     58   72   62   0    73   57   60                                10      60     42   52   48   0    69   86   57                                5       48     42   55   33   0    53   57   54                           32   40      92     100  100  89   100  73   100  100                               20      88     100  76   100  100  69   100  69                                10      58     100  79   78   73   42   63   46                                5       58     100  74   67   73   76   100  35                           33   40      100    93   100  100  100  100  100  83                                20      100    53   94   100  96   64   100  61                                10      100    33   61   68   87   42   91   28                                5       100    3    44   53   69   31   83   11                           34   40      100    100  100  100  100  100  100  86                                20      100    50   100  100  87   76   100  61                                10      100    43   72   65   64   64   74   28                                5       100    13   33   38   0    24   74   6                            35   40      100    80   100  100  100  76   100  92                                20      100    60   69   100  100  44   89   23                                10      100    35   27   38   11   7    100  0                                 5       90     30   8    23   0    0    83   0                            36   40      100    90   100  100  100  87   100  62                                20      100    60   58   100  100  42   89   38                                10      90     45   62   69   42   4    78   8                                 5       71     30   38   31   0    0    78   0                            37   40      54     42   59   61   100  51   47   52                                20      50     26   56   61   20   31   60   35                                10      50     16   59   44   0    42   13   29                                5       46     26   30   44   100  11   27   23                           38   40      90     35   8    46   0    33   100  26                                20      33     30   0    23   0    7    89   0                                 10      48     20   0    15   0    0    39   0                                 5       5      10   0    8    0    0    56   0                            39   40      54     42   85   61   100  42   80   32                                20      42     68   63   61   100  31   100  23                                10      33     79   48   61   24   31   87   16                                5       42     42   41   42   0    24   73   16                           40   40      100    53   100  89   100  53   100  48                                20      92     26   89   42   100  24   87   32                                10      75     16   59   47   100  0    60   48                                5       54     5    4    33   0    0    40   0                            41   40      100    68   100  93   100  64   60   65                                20      58     42   100  59   100  51   33   48                                10      58     16   78   56   100  0    60   32                                5       54     16   56   22   0    0    40   10                           42   40      90     38   100  68   100  67   100  18                                20      52     13   56   32   100  31   100  14                                10      33     19   35   11   42   4    38   22                                5       24     31   24   7    0    0    23   14                           43   40      100    0    22   24   0    24   91   17                                20      100    0    17   24   0    11   65   6                                 10      100    0    0    18   0    0    70   0                                 5       80     0    0    13   0    0    61   0                            44   40      100    100  100  100  100  100  100  100                               20      100    100  100  93   100  96   100  92                                10      62     100  100  71   100  80   100  56                                5       52     100  76   54   100  82   100  36                           45   40      54     31   59   11   100  42   100  0                                 20      25     6    38   0    69   13   63   12                                10      0      0    3    0    42   0    0    0                                 5       4      0    9    0    0    0    0    0                            46   40      100    100  100  100  100  100  100  100                               20      100    90   81   100  87   64   100  46                                10      81     70   76   77   40   56   89   0                                 5       71     35   19   38   0    27   67   0                            47   40      88     100  100  89   100  78   100  77                                20      92     100  100  100  100  69   100  46                                10      92     50   82   78   100  47   88   38                                5       92     38   82   78   71   58   75   27                           48   40      100    100  100  100  100  76   100  100                               20      100    100  94   100  100  64   100  50                                10      92     50   88   67   42   24   63   33                                5       88     38   82   56   78   64   100  29                           49   40      100    67   100  74   100  64   100  64                                20      100    34   75   53   96   42   100  33                                10      100    7    33   38   87   24   100  17                                5       100    0    14   29   47   9    74   3                            50   40      63     100  100  100  100  47   100  100                               20      54     63   94   11   47   13   100  73                                10      21     38   47   0    0    0    38   54                                5       33     25   59   11   20   42   75   58                           51   40      90     100  100  100  100  100  100  100                               20      81     100  92   92   91   82   100  85                                10      75     85   92   77   31   56   100  26                                5       52     60   69   46   0    20   78   8                            52   40      90     100  100  100  100  100  100  77                                20      90     100  100  100  100  64   100  88                                10      71     90   81   77   60   64   89   46                                5       52     80   65   58   4    33   100  15                           53   40      100    100  100  67   100  76   100  65                                20      67     100  100  78   100  76   100  71                                10      42     68   89   75   82   53   100  61                                5       38     42   63   69   20   53   27   45                           54   40      100    20   64   65   87   71   100  50                                20      100    20   53   56   71   42   73   33                                10      100    30   50   53   60   42   91   28                                5       70     27   49   50   42   38   43   14                           55   40      100    20   61   53   47   53   100  28                                20      100    17   56   51   33   31   91   22                                10      100    13   50   59   64   56   100  11                                5       100    0    42   41   42   33   100  0                            56   40      100    100  100  100  100  100  100  100                               20      81     100  100  100  100  100  100  100                               10      71     100  78   67   67   78   100  38                                5       52     70   69   38   0    33   67   26                           57   40      90     100  100  61   100  78   100  78                                20      90     100  100  71   100  80   100  78                                10      90     100  82   61   60   69   100  56                                5       71     88   68   46   42   53   100  42                           58   40      43     44   71   50   13   64   69   61                                20      43     56   68   29   0    53   69   42                                10      48     56   65   54   24   58   54   44                                5       48     56   56   43   13   56   54   44                           59   40      57     56   74   50   29   69   100  61                                20      57     69   59   50   0    33   100  47                                10      52     56   68   61   0    24   100  42                                5       48     50   71   50   0    33   100  28                           60   40      52     75   71   64   13   56   100  47                                20      52     56   65   43   0    42   69   44                                10      43     50   71   43   0    31   77   36                                5       33     63   56   32   9    42   100  33                           61   40      42     0    85   44   100  47   100  52                                20      25     23   59   50   100  33   100  32                                10      29     46   19   42   42   13   33   23                                5       33     16   7    28   31   0    13   6                            Captan                                                                              40      --     44   --   --   0    0    65   --                                20      --     48   --   --   0    0    62   --                                10      --     33   --   --   0    0    46   --                                5       --     19   --   --   0    0    18   --                           Chlorothalonil                                                                      40      75     88   82   48   100  73   95   96                                20      38     76   76   41   100  53   73   71                                10      50     41   70   15   31   40   59   63                                5       44     41   67   26   0    31   50   63                           ______________________________________                                    

                                      TABLE III                                    __________________________________________________________________________     RESULTS OF PLANT TESTS                                                                                          Efficacy                                      Percent Disease Control          Index                                                      Curative        Seed/Soil                                         Foliar                Sugar      Cucumber                                          Tomato       Bean Beet   Bean                                                                               Damping-                                      CPD Late Bean                                                                               Bean                                                                               Powdery                                                                             Leaf                                                                               Rice                                                                              Root                                                                               off                                           No. Blight                                                                              Rust                                                                               Rust                                                                               Mildew                                                                              Spot                                                                               Blast                                                                             Rot Complex                                       __________________________________________________________________________     1   0    0   0   0    0   0  0   0                                             2   0    100 0   100  0   0  100 89                                            3   50   100 0   0    0   0  80  88                                            4   0    100 75  100  0   95 0   44                                            5   0    100 0   0    0   75 50  0                                             6   0    0   90.sup.c                                                                           100  0   0  0   33                                            7   100  100 0   0    75  0  98  33                                            8   90   100.sup.b                                                                          0   0    0   0  0   0                                             9   90   98  0   0    75  90 0   76                                            10  100  100 0   0    95  0  0   122                                           11  100  0   0   100  0   0  0   100                                           12  100  100 0   50   95  75 0   71                                            13  98   100.sup.b                                                                          90.sup.b                                                                           100  98  0  75  0                                             14  0    0   100 50   0   0  90  76                                            15  100  100 90.sup.c                                                                           100  0   95 0   133                                           16  0    90  0   0    95  90 0   0                                             17  100  100 100 100  95  0  0   0                                             18  50   100 0   100  98  0  DP.sup.a                                                                           0                                             19  0    0   100 DP.sup.a                                                                            0   0  0   0                                             20  0    100 0   100.sup.b                                                                           95  0  75  0                                             21  50   100 0   100  100 85 0   77                                            22  0    100 0   100  0   0  0   100                                           23  0    100 0   0    100 0  0   94                                            24  98   100 0   100  50  95 0   100                                           25  100  100 0   100  50  0  0   105                                           26  0.sup.c                                                                             0   0   0    95  0  0   0                                             27  98   0   0   0    95  95 0   83                                            28  90   0   0   50   0   0  95  0                                             29  100  0   0   0    95  0  0   94                                            30  0    100 0   100  0   0  0   0                                             31  0    0   0   100  0   0  0   0                                             32  0    90  0   90   90  0  0   95                                            33  0    100 0   95   0   0  95  0                                             34  0    85  0   95   0   0  0   0                                             35  100  100 0   0    --  0  --  --                                            36  90   100 0   0    --  95 --  13                                            37  0    100 0   0    --  0  --  --                                            38  0    0   100 0    --  0  --  --                                            39  0    98  0   0    --  0  --  --                                            40  75   98  0   0    --  0  --  --                                            41  90   0   0   0    --  0  --  --                                            42  0    100 0   0    0   0  90  111                                           43  0    0   0   0    90  0  0   90                                            44  0    100 0   100  0   0  90  111                                           45  0    95  0   0    90  0  90  65                                            46  75   0   0   0    --  0  --  --                                            47  95   0   0   0    90  90 95  105                                           48  98   100 0   0    DP.sup.a                                                                           50 95  80                                            49  90   100 0   0    0   0  0   100                                           50  0    90  0   0    50  90 0   0                                             51  90   0   0   0    --  0  --  --                                            52  50   0   0   75   --  95 --  --                                            53  98   100 0   0    --  0  --  --                                            54  0    100 0   0    0   0  0   0                                             55  90   100.sup.b                                                                          0   50   95  50 0   0                                             56  95   0   100 0    --  0  --  --                                            57  0    100 0   100  90  0  0   0                                             58  0    100 0   50   0   0  0   0                                             59  0    0   0   DP.sup.a                                                                            0   0  0   0                                             60  0    100 0   DP.sup.a                                                                            0   0  0   0                                             61  0    100 0   0    --  0  --  --                                            __________________________________________________________________________      .sup.a DP = Dead Plant                                                         .sup.b Slight Phytotoxicity                                                    .sup.c Marginal Disease                                                   

We claim:
 1. A compound of the formula ##STR4## in which X is naphthoxy or substituted phenoxy having the formula ##STR5## wherein each R group is a substituent independently selected from the group consisting of lower alkyl, halo, hydroxy, lower alkoxy, nitro, cyano, amino, carboxyl, lower acyl, lower acylamino, lower alkoxycarbonyl, carboxy(lower)alkyl, lower alkylureido, phenylureido, trihalomethyl, cyano(lower)alkyl, phenyl(lower)alkoxycarbonyloxy, lower alkylaminocarbonyloxy, phenylaminocarbonyloxy, lower alkylthio, lower alkylsulfinyl and lower alkylsulfonyl, wherein n has a value of 1 to 3 inclusive, except when each R is halogen when n has a value of 1 to 5 inclusive.
 2. The compound of claim 1 in which R is independently selected from the group consisting of lower alkyl and halo.
 3. The compound of claim 2 in which each R is halogen.
 4. The compound of claim 3 in which each R is chlorine.
 5. The compound of claim 2 in which each R is lower alkyl.
 6. The compound of claim 5 in which each R is methyl. 